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This page provides quick links to all chapters and figures in Essentials of Glycobiology, fourth edition, which includes links for downloadable slides. All links are part of a free, public resource available on the NCBI website. Each link below opens a separate page with the figure, legend, reference information, and the link to the downloadable slide. Please follow appropriate academic attribution and copyright conventions for nonprofit use only. Most of the figures were originally drawn or redrawn by Dr. Richard Cummings (Illustrations Editor). These figures are deliberately downsized in quality for on-screen presentation. For access to and permission to reproduce high-quality figures, contact Cold Spring Harbor Laboratory Press.

Chapters & Figures

Chapter 1 Historical Background and Overview

Figure 1.1 Nobel Laureates
Table 1.1 General Principles of glycobiology
Figure 1.2 Open-chain and ring forms of glucose
Figure 1.3 Schematic representation of the Thy-1 glycoprotein
Figure 1.4 Examples of electron micrographs of glycans coating cell surfaces
Figure 1.5 Examples of symbols and conventions for drawing glycan structures
Figure 1.6 Common classes of animal glycans
Figure 1.7 Glycan-protein linkages reported in nature
Figure 1.8 Biosynthesis, use and turnover of a common monosaccharide

Chapter 2 Monosaccharide Diversity

Figure 2.1 Structures of glyceraldehyde and dihydroxyacetone
Figure 2.2 D- and L-glucopyranose in Fischer projection and chair conformation
Figure 2.3 Fischer projections for the acyclic forms of the D series of aldoses
Figure 2.4 Common monosaccharides found in vertebrates
Figure 2.5 Cyclization of acyclic D-glucose to form pyranose and furanose structures
Figure 2.6 Conversion from Fischer to Haworth projection
Figure 2.7 Chair conformations
Figure 2.8 Conversion from Fischer projection formula

Chapter 3 Oligosaccharides and Polysaccharides

Figure 3.1 Examples of branched structures in N- and O-linked glycans
< class="ms-rteStyle-Accent1">Figure 3.2 style="font-size: 9pt; font-family: arial, sans-serif; background-image: initial; background-position: initial; background-size: initial; background-repeat: initial; background-attachment: initial; background-origin: initial; background-clip: initial;">Repeating units from cellulose and starch showing conformation and glycosidic torsion angles ϕ and ψ
Figure 3.3 Structures of disaccharide repeating units of different glycosaminoglycans and the conformations of monosaccharides from <>heparan sulfate
Figure 3.4 Schematic representation in SNFG (Symbol Nomenclature for Glycans) format of repeating units of bacterial polysaccharides
Table 3.1 Oligosaccharides and polysaccharide repeating units

Chapter 4 Cellular Organization of Glycosylation

Figure 4.1 Initiation and maturation of the major types of eukaryotic glycoconjugates in relation to subcellular trafficking in the ER-Golgi-plasma membrane pathway
Figure 4.2 Topology and localization of Golgi glycosylation enzymes

Chapter 5 Glycosylation Precursors

Table 5.1 Activated sugar donors in animal cells
Figure 5.1 Biosynthesis and interconversion of monosaccharides
Figure 5.2 Biosynthesis of UDP-xylose and the branched sugar donor UDP-apiose from UDP-GlcA
Figure 5.3 Conversion of activated sugar donors
Figure 5.4 Some known transporters for nucleotide sugars, PAPS, and ATP are located in the Golgi membranes of mammals, yeast, protozoa, and plants
Table 5.2 Nucleotide transport in Golgi and ER
Table 5.3 Donors for glycan modifications

Chapter 6 Glycosyltransferases and Glycan-Processing Enzymes

Figure 6.1 The strict acceptor substrate specificity of glycosyltransferases is illustrated by the human B blood group α1-3 galactosyltransferase
Table 6.1 Amino acid-consensus sequences or glycosylation motifs for the formation of glycopeptide bonds
Figure 6.2 Human chorionic gonadotropin showing the determinants of recognition used by glycoprotein hormone N-acetylgalactosaminyl (GalNAc) transferase
Figure 6.3 Sialyl motifs. Domain structure of a typical sialyltransferase, showing the sialyl motifs shared by this family of enzymes
Figure 6.4 Ribbon diagrams of representative GT-A, GT-B, GT-C, and lysozyme-type fold glycosyltransferases
Figure 6.5 Schematic representation of inverting and retaining catalytic mechanisms
Figure 6.6 Catalytic site of bovine β1-4 galactosyltransferase

Chapter 7 Biological Functions of Glycans

Figure 7.1 General classification of the biological functions of glycans
Figure 7.2 Approaches for elucidating the biological functions of glycans

Chapter 8 A Genomic View of Glycobiology

Figure 8.1 Schematic examples of modular glycosyltransferases

Chapter 9 N-Glycans

Figure 9.1 Types of N-glycans
Figure 9.2 Dolichol phosphate (Dol-P)
Figure 9.3 Synthesis of Dolichol-P-P-GlcNAc2Man9Glc3
Figure 9.4 Processing and maturation of an N-glycan
Figure 9.5 Branching and core modification of complex N-glycans
Figure 9.6 Typical complex N-glycans found on mature glycoproteins.

Chapter 10 O-GalNAc Glycans

Figure 10.1 A simplified model of a large secreted mucin
Table 10.1 O-GalNAc glycan cores and antigenic epitopes of mucins
Figure 10.2 Biosynthesis of core 1 and 2 O-GalNAc glycans as described in the text. Green lines are protein
Table 10.2 Glycosyltransferases that synthesize O-GalNAc glycans
Figure 10.3 Biosynthesis of core 3 and 4 O-GalNAc glycans as described in the text. Green lines are protein

Chapter 11 Glycosphingolipids

Figure 11.1 Structures of representative glycosphingolipids (GSLs) and glycoglycerolipids
Figure 11.2 Glycosphingolipid (GSL) neutral cores and their designations based on IUPAC Nomenclature
Figure 11.3 Glycosphingolipids are synthesized by stepwise addition of sugars first to ceramide and then to the growing glycans

Chapter 12 Glycosylphosphatidylinositol Anchors

Figure 12.1 General structure of glycosylphosphatidylinositol (GPI) anchors attached to proteins
Figure 12.2 Glycosylphosphatidylinositol (GPI)-biosynthetic pathways of Trypanosoma brucei, Saccharomyces cerevisiae, and mammals.
Figure 12.3 Predicted topologies of the ER-resident components of glycosylphosphatidylinositol (GPI) biosynthesis in mammalian cells
Table 12.1 Components of the core mammalian and Saccharomyces cerevisiae glycosylphosphatidylinositol (GPI)- biosynthetic machinery
Figure 12.4 Features of glycosylphosphatidylinositol (GPI)-anchored proteins and their processing by GPI transamidase

Chapter 13 Other Classes of Eukaryotic Glycans

Table 13.1 Other classes of eukaryotic glycoprotein glycosylation
Figure 13.1 Modifications of epidermal growth factor (EGF) repeats
Figure 13.2 Extracellular domain of a generic Notch receptor showing numerous sites for POFUT1 and POGLUT1 modifications that are evolutionarily conserved in Drosophila Notch, mouse NOTCH1 and NOTCH2, and human NOTCH1 and NOTCH2
Figure 13.3 Notch signaling pathway
Figure 13.4 Modifications of thrombospondin type-1 repeats (TSRs)
Figure 13.5 Biosynthetic pathway for O-mannose glycans
Figure 13.6 Biosynthetic pathway for C-mannosylation and structural details of a C-mannosylation and structural details of a C-mannosylated tryptophan

Chapter 14 Structures Common to Different Glycans

Figure 14.1 N-Glycan synthesis leads to complex N-glycans with branching GlcNAc residues that are
generally extended in glycosylation reactions that may be tissue-specific, developmentally regulated, or even protein-specific
Figure 14.2 Terminal GlcNAc residues are usually galactosylated
Figure 14.3 Blood group i and I antigen synthesis
Figure 14.4 Type-1, -2, and -3 H, A, and B antigens that form the O (H), A, and B blood group determinants on N- and O-glycans
Figure 14.5 Synthesis of H (O), A, and B blood group determinants
Figure 14.6 Type-1 and -2 Lewis determinants
Figure 14.7 Biosynthesis of antigens of the P1PK blood group system: Pk, P, and P1
Figure 14.8 Structure and synthesis of the Galα1-3Gal antigen
Figure 14.9 Structure and synthesis of N-glycans bearing terminal GalNAc, including those with sulfated-GalNAc found on the pituitary hormones lutropin (LH) and thyrotropin (THS), but not on follicle-stimulating hormone (FSH)
Figure 14.10 Synthesis of the human Sda or mouse CT antigen and the glycolipid GM2
Figure 14.11 Synthesis of α2-6 and α2-3 sialic acid on O-glycans and glycolipids by ST3Gal and ST6GalNAc
families of sialyltransferases
Figure 14.12 Structure and synthesis of glycans with α2-8 sialic acids including polySia on N-glycans b y ST8SIA1 to ST8SIA6

Chapter 15 Sialic Acids and Other Nonulosonic Acids

Figure 15.1 Sialic acids (Sias) and other nonulosonic acids (NulOs)
Figure 15.2 Diversity in sialic acid linkages
Figure 15.3 Hierarchical levels of sialome complexity
Figure 15.4 Metabolism of N-acetylneuraminic acid in vertebrate cells
Table 15.1 A few classic examples of sialic acid-binding proteins in nature
Figure 15.5 Examples of legionaminic and pseudaminic acid-containing glycans in bacteria and Archaea, selected from the Bacterial Carbohydrate Structure Database (BCSDB)

Chapter 16 Hyaluronan

Figure 16.1 Hyaluronan consists of repeating disaccharides composed of N-acetylglucosamine (GlcNAc) and
glucuronic acid (GlcA)
Figure 16.2 Hyaluronan biosynthesis by hyaluronan synthase (HAS) occurs by addition of UDP-sugars (UDP- GlcNAc and UDP-GlcA) to the reducing end of the polymer with release of the anchoring UDP. M++ refers to a metal ion cofactor
Figure 16.3 Modular organization of the link module superfamily of hyaluronan-binding proteins
Figure 16.4 The large cartilage chondroitin sulfate (CS) proteoglycan (aggrecan) forms an aggregate with
hyaluronan and link protein
Figure 16.5 Structure of the link module
Figure 16.6 Hyaluronan signaling in health and disease

Chapter 17 Proteoglycans and Sulfated Glycosaminoglycans

Figure 17.1 Proteoglycans consist of a protein core and one or more covalently attached glycosaminoglycan chains
Figure 17.2 Glycosaminoglycans consist of alternating N-acetylated (GlcNAc or GalNAc) or N-sulfated (GlcNS) glucosamine and either a uronic acid (GlcA or IdoA) or galactose (Gal)
Table 17.1 aria-hidden="true">Diversity among known vertebrate proteoglycans
Figure 17.3 Keratan sulfates (KS) contain a sulfated poly-N-acetyllactosamine chain, linked to either asparagine or serine/threonine residues
Figure 17.4 The biosynthesis of chondroitin sulfate (left chain) and heparan sulfate (right chain) is initiated by the formation of a linkage region tetrasaccharide
Figure 17.5 Biosynthesis of chondroitin sulfate/dermatan sulfate involves the polymerization of N-acetylgalactosamine and glucuronic acid units and a series of modification reactions including O-sulfation and epimerization of glucuronic acid to iduronic acid
Table 17.2 Types of chondroitin sulfates

Chapter 18 Nucleocytoplasmic Glycosylation

Figure 18.1 Cellular topography of nucleocytoplasmic glycosylation
Table 18.1 Examples of nuclear or cytoplasmic glycosylation events
Figure 18.2 Mechanism of glycosylation of Skp1 in the cytoplasm of protists

Chapter 19 The O-GlcNAc Modification

Figure 19.1 Many nuclear, mitochondrial, and cytoplasmic proteins are modified by monosaccharides of O-linked β-N-acetylglucosamine (O-GlcNAc)
Figure 19.2 O-GlcNAcylated proteins occur in many different cellular compartments
Table 19.1 Selected O-GlcNAcylated proteins
Figure 19.3 OGlcNAc transferase (OGT) is regulated by multiple complex mechanisms, including transcriptional regulation of its expression, differential mRNA splicing, proteolytic processing, posttranslational modification, and multimerization with itself and other proteins.
Figure 19.4 Elevating O-GlcNAc blocks insulin signaling at many points

Chapter 20 Evolution of Glycan Diversity

Figure 20.1 Circular depiction of phylogeny of cellular forms of life on earth
Figure 20.2 Characteristic pathways of N-glycan processing among different eukaryotic taxa

Chapter 21 Eubacteria

Figure 21.1 Conceptual organization of the cell envelopes of Gram-negative bacteria, Gram-positive bacteria, and mycobacteria
Figure 21.2 Structure, biosynthesis, and inhibition of peptidoglycan assembly
Figure 21.3 Structures of additional cell wall polymers in classical Gram-positive bacteria and mycobacteria
Figure 21.4 Structural organization of lipopolysaccharides (LPSs)
Figure 21.5 Assembly and export of lipopolysaccharides (LPSs)
Figure 21.6 Structures of exopolysaccharides and capsular polysaccharides (CPSs and EPSs)

Chapter 22 Archaea

Figure 22.1 Diversity of archaeal cell wall structures
Figure 22.2 The chemical structure of pseudomurein
Figure 22.3 The structural diversity of N- and O-linked glycans in Archaea
Figure 22.4 The pathway of N-glycosylation in Haloferax volcanii

Chapter 23 Fungi

Figure 23.1 Illustration of the cell wall of yeasts, showing glycan polymers and mannoproteins
Figure 23.2 Structures of selected yeast mannans
Figure 23.3 Structures of selected O-linked glycans in fungi: yeast, filamentous fungi, and Cryptococcus
Figure 23.4 Biosynthesis of N-glycans and their transfer to -Asn-X-Ser/Thr- sequons of newly synthesized glycoproteins in the fungal endoplasmic reticulum (ER)
Figure 23.5 Structures of two fungal glycosylphosphatidylinositol (GPI) anchors
Figure 23.6 A quick-freeze deep-etch image of the edge of a Cryptococcus neoformans cell
Figure 23.7 Structures of capsular polysaccharides in Cryptococcus neoformans

Chapter 24 Viridiplantae and Algae

Figure 24.1 Glycosyl sequences of cellulose, selected hemicelluloses, mixed-linkage glucan, and callose
Figure 24.2 Schematic structure of pectin
Figure 24.3 Schematic structure of proteoglycan referred to as arabinoxylan pectin arabinogalactan protein1 (APAP1)
Figure 24.4 Types of N-glycans identified in plants
Table 24.1 Estimated number of genes encoding proteins involved in the synthesis and modification of glycans in plants and humans
Figure 24.5 Processing of N-glycans in the plant secretory system
Figure 24.6 The most abundant plant galactolipids

Chapter 25 Nematoda

Figure 25.1 Caenorhabditis elegans
Figure 25.2 Life cycle of Caenorhabditis elegans
Figure 25.3 Biosynthesis of paucimannosidic and core fucosylated N-glycans in Caenorhabditis elegans
Figure 25.4 Biosynthesis of core-1 O-glycans in Caenorhabditis elegans and some O-glycans proposed to occur in adult worms
Figure 25.5 Biosynthesis of chondroitin in Caenorhabditis elegans
Figure 25.6 Chondroitin proteoglycans (CPGs) of Caenorhabditis elegans
Figure 25.7 Examples of nematode glycolipids
Figure 25.8 Examples of nematode glycans

Chapter 26 Arthropoda

Figure 26.1 N-Linked glycan diversity in Drosophila and other insects
Table 26.1 Genes that affect the synthesis or function of Drosophila glycans
Figure 26.2 Mutations in enzymes that process complex N-linked glycans alter adult brain morphology in D. melanogaster
Figure 26.3 O-Linked glycan diversity in Drosophila and other insects
Figure 26.4 Cell fate choices dependent on Notch require appropriate glycan expression
Figure 26.5 Glycosaminoglycans regulate the contact-dependent maintenance of germline stem cells (GSCs)
Figure 26.6 Glycosphingolipid glycan diversity

Chapter 27 Deuterostomes

Figure 27.1 The purple sea urchin Strongylocentrotus purpuratus. Sperm binding to a sea urchin egg
Figure 27.2 N-glycan diversity in deuterostomes
Figure 27.3 Zebrafish (Danio rerio). Adult mouse (Mus musculus). Gene editing using CRISPR/Cas9
Figure 27.4 Cre-loxP targeting for making conditional gene knockouts in the mouse

Chapter 28 Discovery and Classification of Glycan-Binding Proteins

Figure 28.1 Representative structures from four common animal lectin families
Figure 28.2 Arrangements of carbohydrate-recognition domains (CRDs) in lectins
Figure 28.3 Several major structural families of glycan-binding proteins (GBPs) and their biological distributions
Figure 28.4 Mechanisms of enhanced binding of natural ligands to lectins

Chapter 29 Principles of Glycan Recognition

Figure 29.1 Monovalent and multivalent interactions of a glycan-binding protein (GBP) with monovalent or multivalent glycan ligands
Figure 29.2 Equations governing the interactions of a glycan-binding protein or lectin (L) with a glycan ligand (G)
Figure 29.3 Example of frontal affinity chromatography, in which different concentrations of a glycan are applied to a column of immobilized GBP
Figure 29.4 Example of isothermal titration calorimetry (ITC)
Figure 29.5 Example of surface plasmon resonance (SPR)
Figure 29.6 Preparation of covalent glycan microarrays printed on N-hydroxysuccinimide (NHS)- or epoxide- activated glass slides

Chapter 30 Structural Biology of Glycan Recognition

Figure 30.1 Graphical representation of six different calcium-dependent carbohydrate-binding sites found in crystal structures of lectins
Figure 30.2 Distribution of the lectins with structures available in the Unilectin3D database as a function of fold family. Graphical representation of some convergent β-propeller folds for lectins
Figure 30.3 Chemical shift mapping of slow and fast exchange binding sites for a 4-sulfated chondroitin sulfate (CS) hexamer on the Link module of TSG6
Figure 30.4 Binding epitope identification in a complex-type glycan bound to the HIV-1 neutralizing antibody PG16 using saturation transfer difference (STD) nuclear magnetic resonance (NMR) information
Figure 30.5 Cryo-electron microscopy structure of the native fully glycosylated HIV-1 envelope trimer
Figure 30.6 Docking of a heparan sulfate (HS) pentamer to the receptor protein tyrosine phosphatase, LAR (PDB entry 2YD5)
Figure 30.7 Stereo view of interactions between the donor (CMP-Neu5Ac), acceptor (GlcNAcβ1-4Gal), and protein residues in the active site of ST6Gal1

Chapter 31 R-Type Lectins

Figure 31.1 The R-type lectin superfamily
Figure 31.2 Structure of ricin
Figure 31.3 Pathway of ricin uptake by cells and mechanism whereby toxic activity of A chain in cytoplasm results in cell death
Figure 31.4 Structures of β-trefoil folds of R-type lectin domains in various proteins
Figure 31.5 Structure and function of UDP-GalNAc:polypeptide α-N-acetylgalactosaminyltransferases (ppGalNAcTs)

Chapter 32 L-Type Lectins

Figure 32.1 Structure of concanavalin A (ConA), a legume seed lectin in complex with a branched pentasaccharide GlcNAcβ1-2Manα1-3(GlcNAcαβ1-2Manα1-6)Man to 2.7 Å.
Figure 32.2 Comparison of the subunit structures of soybean agglutinin complexed with a pentasaccharide containing Galβ1-4GlcNAc-R and human galectin-3 at 1.4 Å complexed with Galβ1-4GlcNAc
Figure 32.3 Three-dimensional structure of a peanut agglutinin (PNA) monomer showing the four loops involved in sugar binding: loops A, B, C, and D
Figure 32.4 Schematic representations of calreticulin (CRT) and calnexin (CNX) showing the lectin domain, the P domain (containing the proline repeats), and the calcium-binding domain (A,B)

Chapter 33 P-Type Lectins

Figure 33.1 Cross-correction of lysosomal enzyme deficiencies in cultured cells
Figure 33.2 Pathways for biosynthesis of N-glycans bearing the mannose 6-phosphate (M6P) recognition marker
Figure 33.3 GlcNAc-P-T is an α2β2γ2 hexamer encoded by two genes
Figure 33.4 (A) Schematic diagram of cation-independent (CI-MPR) and cation-dependent mannose 6-phosphate receptors (CD-MPR). (B) Ribbon diagram of the bovine CD-MPR.
Figure 33.5 Subcellular trafficking pathways of glycoproteins, lysosomal enzymes, and M6P receptors (MPRs)

Chapter 34 C-Type Lectins

Figure 34.1 Structure of C-type lectins (CTLs)
Figure 34.2 Crystal structure of trimeric rat mannose-binding protein-A complexed with α-methylmannoside
Figure 34.3 Different groups of C-type lectins (CTLs) and their domain structures
Figure 34.4 Some C-type lectins (CTLs) are endocytic receptors
Figure 34.5 Signaling activity of C-type lectins (CTLs) in innate immune responses
Figure 34.6 Structures and functions of selectins

Chapter 35 I-Type Lectins

Figure 35.1 Domain structures of the known Siglecs in humans and mice
Figure 35.2 Structural basis of Siglec binding to ligands
Figure 35.3 Proposed biological functions mediated by CD22
Figure 35.4 Probable evolutionary chain of Red Queen effects involving Sias and CD33rSiglecs
Figure 35.5 Proposed biological functions mediated by CD33-related Siglecs

Chapter 36 Galectins

Figure 36.1 Different types of galectins in vertebrates and invertebrates and their organization and sequences
Figure 36.2 (A) Ribbon diagram of the crystal structure of human galectin-1 complexed with lactose. (B) A highlight of the interactions of key amino acid residues within the CRD with bound lactose, and the partial sequence of the CRD in human galectin-1. (C) Primary sequence of human galectin-1 with residues numbered and corresponding to those in the crystal structure
Figure 36.3 Structural aspects of galectins from mammals and invertebrates
Figure 36.4 Possible biosynthetic routes for galectins in animal cells, using galectin-1 as an example
Figure 36.5 Functional interactions of galectins with cell-surface glycoconjugates and extracellular glycoconjugates leads to cell adhesion and cell signaling

Chapter 37 Microbial Lectins: Hemagglutinins, Adhesins, and Toxins

Figure 37.1 Structure of the influenza virus hemagglutinin (HA) ectodomain
Table 37.1 Examples of viral lectins and hemagglutinins
Figure 37.2 Two views of a putative heparin sulfate-binding site on the dengue virus envelope protein
Figure 37.3 Escherichia coli express hundreds of pili, indicated by the fine filaments extending from the bacterium
Figure 37.4 The α anomer of mannose in the binding site of FimH
Table 37.2 Examples of interactions of bacterial adhesins with glycans
Figure 37.5 Crystal structure of cholera toxin B-subunit pentamer bound to GM1 pentasaccharide
Table 37.3 Examples of glycan receptors for bacterial toxins
Table 37.4 Examples of glycan receptors for parasites

Chapter 38 Proteins That Bind Sulfated Glycosaminoglycans

Table 38.1 Examples of various classes of glycosaminoglycan (GAG)-binding proteins
Table 38.2 Methods to measure glycosaminoglycan (GAG)-protein interaction
Figure 38.1 Conformation of heparin oligosaccharides
Figure 38.2 Crystal structure of the antithrombin-pentasaccharide complex (from Protein Data Bank) and interactions between key amino acid residues and individual elements in the pentasaccharide
Figure 38.3 Crystal and solution structures of GAG-protein complexes

Chapter 39 Glycans in Glycoprotein Quality Control

Figure 39.1 Mature N-glycan
Figure 39.2 Model of quality control in glycoprotein folding
Figure 39.3 Degradation of oligomannosyl N-glycans in the endoplasmic reticulum (ER), cytoplasm, and lysosomes

Chapter 40 Free Glycans as Bioactive Molecules

Figure 40.1 Plant defense responses upon glycan perception by pattern-recognition receptors (PRRs)
Figure 40.2 Oligosaccharins that are active in plants. Examples of oligosaccharides derived from fungal, oomycete, and plant cell walls are shown
Figure 40.3 Generic structure of a Nod factor

Chapter 41 Glycans in Systemic Physiology

Chapter 42 Bacterial and Viral Infections

Figure 42.1 Classical experiments on the role of the pneumococcal polysaccharide capsule in virulence
Figure 42.2 Activation of immune signaling by bacterial lipopolysaccharide (LPS)
Figure 42.3 Examples of mechanisms of bacterial adherence to host cell surfaces
Figure 42.4 Structure of a polymicrobial biofilm
Figure 42.5 Mechanisms of viral entry into host cells

Chapter 43 Parasitic Infections
Table 43.1 Worldwide distributions of some major parasitic human diseases
Table 43.2 Some of the major parasitic protozoans of humans
Table 43.3 Some of the major parasitic helminths of mammals
Figure 43.1 Life cycle of Plasmodium falciparum, a parasitic protozoan that causes the most severe form of malaria in humans
Table 43.4 Some major parasites and their glycan-binding proteins
Figure 43.2 Schematic representation of the major surface glycoconjugates of procyclic and metacyclic Trypanosoma brucei
Figure 43.3 Schematic representation of the major surface glycoconjugates of Trypanosoma cruzi
Figure 43.4 Life cycle of Leishmania species, the parasitic protozoan that causes leishmaniasis in humans
Figure 43.5 Schematic representation of the major cell-surface glycoconjugates of Leishmania
Figure 43.6 Structure of Entamoeba histolytica lipopeptidophosphoglycan (LPPG)
Figure 43.7 Life cycle of Schistosoma species, the parasitic helminth that causes schistosomiasis in humans
Figure 43.8 Examples of structures of glycans found in parasitic helminths, including Schistosoma mansoni and Haemonchus contortus

Chapter 44 Genetic Disorders of Glycan Degradation

Figure 44.1 Degradation of complex-type N-glycans
Table 44.1 Defects in glycoprotein degradation-the glycoproteinoses
Table 44.2 Defects in glycosaminoglycan (GAG) degradation-the mucopolysaccharidoses
Table 44.3 Defects in glycolipid degradation
Figure 44.2 Degradation of hyaluronan and heparan sulfate (HS)
Figure 44.3 Degradation of chondroitin/dermatan sulfates (CS/DS) and keratan sulfate (KS)
Figure 44.4 Degradation of glycosphingolipids

Chapter 45 Genetic Disorders of Glycosylation

Figure 45.1 Glycosylation-related disorders
Table 45.1 Selected congenital disorders of glycosylation in humans
Figure 45.2 Congenital disorders of glycosylation in the N-glycosylation pathway
Figure 45.3 O-Man glycan biosynthetic pathway
Figure 45.4 CDGs related with UDP-Gal metabolism
Figure 45.5 Golgi homeostasis defects

Chapter 46 Glycans in Acquired Human Diseases

Chapter 47 Glycosylation Changes in Cancer

Figure 47.1 N-Glycans increase in size on neoplastic transformation of cells, in part because of increased MGAT4 and MGAT5 activity, which catalyzes GlcNAc branching of N-glycans
Figure 47.2 Loss of normal topology and polarization of epithelial cells in cancer results in secretion of mucins with truncated O-GalNAc glycans, such as sialyl-Tn (STn) and Tn, into the bloodstream
Figure 47.3 Gangliosides expressed in human neuroectodermal tumors
Figure 47.4 In normal physiology platelets, leukocytes and endothelial cells interact via selectins and selectin ligands
Figure 47.5 Glycosaminoglycans (GAGs) in cancer

Chapter 48 Glycan-Recognizing Probes as Tools

Figure 48.1 Examples of N-glycans recognized by concanavalin A (ConA) from Canavalia ensiformis and Galanthus nivalis agglutinin (GNA)
Figure 48.2 Examples of types of N-glycans recognized by L-PHA, E-PHA, and DSA
Figure 48.3 Examples of types of glycan determinants bound with high affinity by different plant and animal lectins
Figure 48.4 Examples of types of glycan determinants bound with high affinity by different plant lectins
Figure 48.5 Examples of different mammalian glycan antigens recognized by specific monoclonal antibodies
Figure 48.6 Additional examples of different mammalian glycan antigens recognized by specific monoclonal antibodies
Figure 48.7 Examples of different uses of plant and animal lectins, carbohydrate-binding molecules (CBMs), and antibodies in glycobiology
Figure 48.8 An example of the use of different immobilized plant lectins in serial lectin affinity chromatography of complex mixtures of glycopeptides

Chapter 49 Glycosylation Mutants of Cultured Mammalian Cells
Figure 49.1 Alteration of cell-surface glycans by recessive and dominant glycosylation mutations
Figure 49.2 Selections for glycosylation mutants
Figure 49.3 Mutation of UDP-Glc/UDP-GlcNAc-4-epimerase, also called UDP-Gal-4-epimerase or GALE, in ldlD mutant Chinese hamster ovary (CHO) cells prevents the generation of UDP-Gal and UDP-GalNAc preventing addition of Gal and GalNAc to all glycans
Table 49.1 Examples of recessive glycosylation mutants
Table 49.2 Examples of dominant mutants expressing a new activity
Table 49.3 Examples of mutants defective in proteoglycan assembly

Chapter 50 Structural Analysis of Glycans

Figure 50.1 Glycosidases used for structural analysis
Table 50.1 Table of enzymes for glycan analysis
Figure 50.2 An example of linkage analysis showing a bacterial O-linked branched hexasaccharide with a sequence of Rha1-3Glc1-(Glc1-3GlcNAc1-)2,6Glc1-6GlcNAc
Figure 50.3 Sections of 2D 1H-13C 700 MHz NMR spectra of a sialyl Lewis x-capped glycan in D2O
Figure 50.4 Energy plots showing likely ϕ-ψ values for the glycosidic torsion angles between Glc residues in Glcβ1-4Glc-OMe

Chapter 51 Glycomics and Glycoproteomics

Figure 51.1 Analysis of a purified single glycoprotein
Figure 51.2 Glycomics-assisted glycoproteomics of a complex mixture of glycoproteins
Table 51.1 Families of common monosaccharides found in mammalian N- and O-linked glycans
Figure 51.3 Collision-induced dissociation-tandem mass spectrometry (CID-MS/MS) of released N-glycans
Figure 51.4 Complementary tandem mass spectrometry (MS/MS) fragmentation of N-glycopeptides

Chapter 52 Glycoinformatics

Figure 52.1 The critical role of glycomics in systems biology
Table 52.1 Glycoscience databases, repositories and web portals
Table 52.2 Glycoinformatics data analysis software tools

Chapter 53 Chemical Synthesis of Glycans and Glycoconjugates
Figure 53.1 Stereospecific formation of glycosidic bonds as either an α- or β-linkage and formation of a cyclic oxonium ion intermediate leading to the formation of a β-glycosidic linkage
Figure 53.2 Protective group manipulations, which can be carried out in one-pot procedures, toward a series of glucopyranose-derived building blocks for glycan assembly
Figure 53.3 Solution phase synthesis of Pseudomonas aeruginosa-derived decasaccharide 10
Figure 53.4 Schematic overview of automated glycan assembly and automated glycan assembly (AGA) of 100- polymannoside 14 and AGA of an alginate dodecasaccharide
Figure 53.5 Synthesis of a 151-mer polymannoside by block coupling of polymannosides prepared by automated glycan assembly (AGA)
Figure 53.6 One-pot synthesis of octasaccharide antigen 32

Chapter 54 Chemoenzymatic Synthesis of Glycans and Glycoconjugates

Figure 54.1 Formation and hydrolysis of the glycosphingolipid, glucosylceramide
Figure 54.2 Glycosyltransferase-mediated synthesis of sialyl-Lewis x
Figure 54.3 Glycosyltransferase-mediated synthesis of ganglio-oligosaccharides
Figure 54.4 Chemoenzymatic synthesis of a library of mammalian N-glycans
Figure 54.5 Equilibrium in a retaining β-glucosidase and mutant retaining β-glucosidase in which the catalytic nucleophile is substituted for a nonparticipating amino acid allows for the construction of β-glucosides
Figure 54.6 Glycosynthase-mediated synthesis of flavonoid glycosides
Figure 54.7 A combined glycosyltransferase/glycosynthase/chemical synthesis of a lysosphingolipid
Figure 54.8 Glycosynthase mediated synthesis of homogeneous peptide N-glycans

Chapter 55 Chemical Tools for Inhibiting Glycosylation

Figure 55.1 Different classes of compounds for inhibiting glycosylation including those that prevent the formation of biosynthetic precursors, those that directly act on glycosidases and glycosyltransferases, and those that serve as primers/decoys and chain terminators
Figure 55.2 Examples of alkaloids that inhibit glycosidases involved in N-linked glycan biosynthesis
Figure 55.3 Inhibitors of O-GlcNAc-specific β-hexosaminidase (OGA) and O-GlcNAc transferase (OGT)
Table 55.1 Synthetic substrate-based inhibitors of glycosyltransferases
Figure 55.4 Inhibitors of glycosphingolipid metabolism
Figure 55.5 Examples of glycoside primers
Figure 55.6 Structure of neuraminidase inhibitors

Chapter 56 Glycosylation Engineering

Figure 56.1 Overview of species-specific glycosylation features
Table 56.1 Examples of major achievements in glycoengineering of cells
Figure 56.2 Precise gene editing modalities
Figure 56.3 A complex N-glycan with glycosyltransferases responsible for each reaction and a generalized scheme for genetically altering the expression of different classes of glycans on cells

Chapter 57 Glycans in Biotechnology and the Pharmaceutical Industry

Figure 57.1 Examples of natural products that contain glycan components
Figure 57.2 The synthetic influenza neuraminidase inhibitors Relenza and Tamiflu
Table 57.1 Examples of glycan-based drugs, their target diseases, and modes of action
Figure 57.3 Glycomimetic E-selectin inhibitors based on sialyl-Lewis x

Chapter 58 Glycans in Nanotechnology

Figure 58.1 Overview of different types of glyconanomaterials created by coupling glycans to the surface of diverse nanomaterials
Figure 58.2 A calculated representation of a 2-nm-sized gold glyconanoparticle formed by 102 gold atoms and coated with 44 molecules of 5-mercaptopentyl α-D-mannopyranoside and the corresponding transmission electron microscopy (TEM) image.
Figure 58.3 In vitro binding studies using SLex-MNPs to rat E-selectin; magnetic resonance images (MRIs) and their 3D reconstruction of SLex magnetic nanoparticles
Figure 58.4 In vivo localization of filled-and-functionalized glyco-single-walled nanotubules (SWNTs)

Chapter 59 Glycans in Bioenergy and Materials Science

Figure 59.1 The stacking of cellulose chains showing that there are regions of "order" and "disorder" and during one type of cellulose nanomaterial extraction process that uses acid hydrolysis, the disordered regions are preferentially dissolved and only the crystalline regions are left
Figure 59.2 Transmission electron microscopy images showing two types of cellulose nanomaterials

Chapter 60 Future Directions in Glycosciences

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